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The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [ 1 ] [ 2 ] [ 3 ] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.
The Curtius rearrangement (or Curtius reaction or Curtius degradation), first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas.
The Hofmann rearrangement is a decarbonylation reaction whereby an amide is converted to an amine by way of an isocyanate intermediate. It is usually carried out under strongly basic conditions. It is usually carried out under strongly basic conditions.
In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. [1] Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular. In the example below ...
Hock rearrangement; Hofmann bromamide reaction; Hofmann degradation, Exhaustive methylation; Hofmann elimination; Hofmann Isonitrile synthesis, Carbylamine reaction; Hofmann product; Hofmann rearrangement; Hofmann–Löffler reaction, Löffler–Freytag reaction, Hofmann–Löffler–Freytag reaction; Hofmann–Martius rearrangement; Hofmann's rule
The reaction is closely related to the Curtius rearrangement except that in this reaction the acyl azide is produced by reaction of the carboxylic acid with hydrazoic acid via the protonated carboxylic acid, in a process akin to a Fischer esterification.
PIFA can be used to carry out the Hofmann rearrangement under mildly acidic conditions, [11] rather than the strongly basic conditions traditionally used. [ 12 ] [ 13 ] The Hofmann decarbonylation of an N -protected asparagine has been demonstrated with PIDA, providing a route to β-amino- L - alanine derivatives.
Phenyl azide ("diazoamidobenzol"), was prepared in 1864 by Peter Griess by the reaction of ammonia and phenyldiazonium. [2] [3] In the 1890s, Theodor Curtius, who had discovered hydrazoic acid (HN 3), described the rearrangement of acyl azides to isocyanates subsequently named the Curtius rearrangement. [4]